Rep. Alexandria Ocasio-Cortez’s outspoken optimal aide, Saikat Chakrabarti, is making waves in Washington v his difficult talk—but friends and also former partner from the tech human being have fond storage of working v him in ~ Stripe and also Mockingbird, the website design firm he cofounded.

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Rep Alexandria Ocasio-Cortez, D-N.Y., pipeline a news conference in the Capitol Visitor facility after responding to an adverse comments by president Trump the were directed at the freshman house Democrats on Monday, July 15, 2019. She chief the staff, Saikat Chakrabarti, shows up at left.
One previous colleague defines him as “smart however has very tiny ego.” an additional praises him together “a an extremely soft-spoken, genuine, kind human being.” and a third compliments him as being “the nicest, most purely urged guy in the world.”

It may be tough to believe, but they’re describing Saikat Chakrabarti, the hard-hitting chef of employee to Rep. Alexandria Ocasio-Cortez, who’s been making tide in Washington of late v his dull rhetoric and take-no-prisoners attitude.

Over Twitter, he’s drawn ire by railing versus Speaker Nancy Pelosi by name, sarcastically calling she a “legislative mastermind.” He’s labeling moderate members that his party as modern equivalents of the “Southern Democrats” the the 1940s, referring to the faction committed to maintain segregation and also opposing civil rights. He’s offered “New Democrats” and “Blue Dogs” together seemingly disparaging terms because that Ocasio-Cortez’s much more centrist colleagues.

But the was once he lambasted a congresswoman for sustaining a weaker border assist package that the House autonomous Caucus responded, via that Twitter account: “Who is this guy?”

It’s jealousy, claims political consultant Zack Exley. “They’re all just really jealousy of him because he’s AOC’s chief of staff,” added Exley, a previous colleague and also close friend of Chakrabarti. “They’re additionally really angry because he, and also she, speak their mind and also call the end bullshit as soon as they watch it.”

But, seriously, “Who is this guy?”

Saikat Chakrabarti was raised in ft Worth by Bengali-American immigrant parents. The leap native a working-class high school in Texas to Harvard to be formidable, says Exley, and the juxtaposition of the elite with the humble was likely very early shaper of his politics views.

“Humbleness” is a thread the runs with all the personality testimonies from friends and colleagues. That’s the top quality that they say permits him to operate sanely in politics—and that permitted him to carry out the same formerly in Silicon Valley, where he an initial made his mark. “I’m harping on around this humbleness, but it’s rarer here than you could think,” claims ex-colleague Diede van Lamoen, that the tech world.

Chakrabarti and van Lamoen functioned together in ~ Stripe, a payment management agency whose client now include Lyft, Target, and also Unicef. Back then, Chakrabarti was among the beforehand engineers, and probably the third employee, recalls Ross Boucher, that was the fifth. The 2 were component of a team the spent seven months, before the company’s start in September 2011, designing and building every the user-facing parts of Stripe: the dashboard, the API, the subscription features, the website itself. “I think it’s fair to say that Saikat had actually a far-reaching impact top top the direction the the firm and absolutely on its early on success,” Boucher says.

The work-life balance was almost nonexistent then. Boucher and also Chakrabarti would eat every enjoy the meal together—in the office. They’d work out in ~ the gym together and then go back to the office. As if the burnout weren’t enough, the was additionally operating a separate tech company, together with Sheena Pakanati, his college friend, onetime roommate—and, oh, that fourth Stripe employee.

That firm was Mockingbird, a web-based device for making websites and apps the the two cofounded shortly before Stripe and managed v their time there. (It’s still around, yet Chakrabarti is no longer involved.) “Mockingbird, at the time, was regarded as a really high-quality product and also was yes, really respected by the market,” says van Lamoen, including that the two articulated that they wished they’d done more with it.

But, life happened. A far-reaching job possibility for his wife, Kami, take it the pair to London in 2013, i beg your pardon is wherein van Lamoen, then Stripe’s head of international, opened up shop together a base for an international expansion. Chakrabarti continued his Stripe job-related in the U.K. Because that a couple of months before calling that quits. Hemingway had actually his Paris era. Bowie had actually his Berlin era. Chakrabarti had actually a London era, which came to be his soul-searching period.

The introspection led to a standard self-reflective conundrum: Is this really all there is? “He wasn’t satisfied by the tech scene,” van Lamoen says. “There to be the feeling that this doesn’t have enough meaning.” Besides, in the London satellite office, he perhaps no longer felt together integral to the team. And yet, that still feel the pressures of the Valley’s constraining ethos.

The change from tech right into politics, then, appeared a press rather than a pull. “I don’t think there was a understand plan,” claims Pakanati of she friend’s chiseling out his new path, “but quite a collection of exploratory steps.” The very first of these procedures would be to contact Zack Exley about joining Bernie Sanders’s 2016 presidential campaign.

One the the first things Exley asked, together he did v every misguided naïf who inquired about hopping top top board: “Why execute you desire to ruin your career by functioning for Bernie?” half joking, but fifty percent serious, that told me, “It was construed that if friend were functioning for Bernie, you might get blacklisted.”

Furthermore, Exley to be skeptical since Silicon valley personnel would constantly hassle him v hopeless offers. “I know specifically what friend need,” they’d tell him. “You need an app that go x, y, or z, or every little thing idea that’s to be tried a million times and also doesn’t work.” yet Chakrabarti was different. That listened. He participated.

Mr. Chakrabarti goes to Washington (well, Burlington, actually)

Exley claims the recent Valley dropout acquired to work as one organizer, sitting down through volunteers and also attending events: “He really dug to number out what we were trying come accomplish.” At the point, his tech prowess materialized for the very first time in the political field, as he developed tech devices to aid simplify campaign paperwork, like occasion invite lists. His small tweaks would conserve 100 steps, Exley says. “He did a million tiny things favor that. And also that’s what allowed everything come scale.”

Separately, Chakrabarti would certainly team up v Pakanati again to build Spoke, another tool that smoothed campaign organization. It’s a peer-to-peer texting tool that streamlines text post alerts because that supporters and also organizers. The Bernie campaign used it, and because it’s open-source software, it’s been employed ~ above a national and global scale: to engage voters in congressional gyeongju in Alabama and Virginia, come mobilize for the Affordable care Act, and for the poll to accomplish marriage equality in Australia. In 2017, the duo moved ownership of speak to the steady advocacy group,

As v Mockingbird, there were clues of regret the they can have done more with Spoke. “Things simply went in a various direction, so us didn’t finish up emerging the company,” Pakanati says. For Chakrabarti, the direction to be moving more firmly right into politics. If that was, then, in the middle of the Venn chart that included tech and also progressive politics, his trajectory was taking him into the fuller one of the latter.

With Exley, he’d walk on to uncovered two different PACs: Brand brand-new Congress and Justice Democrats. Exley says the brainwave for the former happened while they to be lounging roughly in las Vegas during the Nevada caucus, wondering what they’d execute after the election. Brand brand-new Congress, castle decided, would certainly serve as a “post-partisan” committee come endorse steady candidates during a Hillary Clinton presidency.

But as soon as the election visited Trump, righteousness Democrats came to be a much better model, in that its core aim to be to defeat the Republican Party—”which had actually gone off the deep end”—and to press for a communication that had securing the Green new Deal, life wages, and also Medicare because that all. The PAC endorsed 79 steady candidates in the 2018 midterms, consisting of the 4 congresswomen now known by fans and adversaries alike together “The Squad“: Ilhan Omar, Rashida Tlaib, Ayanna Pressley and Alexandria Ocasio-Cortez. Chakrabarti would come to be the latter’s project chair, and also then she chief of staff.

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Even if AOC’s right-hand man has actually physically left the tech world, his partner think the job-related ethic and discipline he occurred early on make him a rare example of humility in politics. “I always joke the he was the one emotionally healthy and balanced person in politics,” Exley says of Chakrabarti’s time as executive director of your PACs. “He come from an setting where civilization actually did job-related all day, and had meetings and also made decisions. And that’s not specifically how progressive campaigns constantly work.”

For Exley, his friend’s provocative tweets room coming indigenous a ar of deep care about the state the the country. So, why room they taking residence members by surprise? “A many these people in Congress have actually just been behaving badly for so countless years without anyone calling lock out,” Exley says. “The human being on the Hill that room upset with him can’t number out his motives, because they’re like, ‘what’s this man after?’ castle can’t think he simply wants to do Congress work much better and be much less corrupt and fix stuff.”

Whatever you do of the back and forth, Chakrabarti’s transition out the tech appears to have actually been a singular success. “He’s among the very couple of people the has broken out of tech in a structural way, gone on a fully different path, and also remade a success,” van Lamoen says. “A lot of of people talk about doing that. Very few follow through.”

Chakrabarti, in flawless following with his understood affability, decreased to talk since of household commitments—but was very polite around it.